Triethylamine → HCID 14859978, compound

HRID 260160Notes

Reaction equation

HRID 260160 reaction equation
[C:1]([O:20][C@@H:21]1[C@@H:25]([CH2:26][O:27][C:28]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:24][C@@H:23]([N:47]2[C:56]3[N:55]=[CH:54][N:53]([CH2:57][C:58]4[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=4)[C:51](=[O:52])[C:50]=3[N:49]=[CH:48]2)[C@@H:22]1[OH:64])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[S:72](Cl)([C:75]([F:78])([F:77])[F:76])(=[O:74])=[O:73]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:1]([O:20][C@@H:21]1[C@@H:25]([CH2:26][O:27][C:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:24][C@@H:23]([N:47]2[C:56]3[N:55]=[CH:54][N:53]([CH2:57][C:58]4[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=4)[C:51](=[O:52])[C:50]=3[N:49]=[CH:48]2)[C@@H:22]1[O:64][S:72]([C:75]([F:78])([F:77])[F:76])(=[O:74])=[O:73])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 79000Trifluoromethanesulfonyl chlorideHCID 14859974HCID 14859974, compound

Product 1

HCID 14859978HCID 14859978, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3',5'-di-O-trityl-1-benzylinosine (2.0 g, 2.4 mmol), 4-dimethylaminopyridine (290 mg, 2.4 mmol) and triethylamine (480 mg, 4.8 mmol) in methylene chloride (40 mL) is added triflyl chloride (800 mg, 4.8 mmol), and the mixture is stirred at room temperature for 1 hour, and then concentrated in vacuo. The residue is chromatographed on a silica gel column using a mixture of tetrachloromethane and ethyl acetate (5:1 v/v) as the eluent to give 3',5'-di-O-trityl-2'-O-triflyl-1-benzylinosine as a foam (1.82 g, 78% yield), 1H NMR (Me2SO-d6) δ 2.92-2.96 (2H, m, H-5',5"), 3.62-3.69 (1H, m, H-4'), 4.41-4.43 (1H, m, H-3'), 5.23 (2H, s, CH2Ph), 5.89-5.95 (1H, m, H-2'), 6.66 (1 H, d, H-1', J1',2' =6.3 Hz), 7.18-7.34 (35H, m, 2 x Tr and CH2Ph), 8.29, 8.32 (1H each, s, H-2, H-8). Analyses calculated for C56H45F3N4O5S: C, 68.98, H, 4.65, N, 5.63. Found: C, 68.94, H, 4.76, N, 5.63.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue is chromatographed on a silica gel column
  3. additiona mixture of tetrachloromethane and ethyl acetate (5:1 v/v) as the eluent

Sources & evidence

ORD record
ord-acd234bc08974292998b4cf455243a8f
Source dataset
uspto-grants-1996_06
Patent number
US05525720

Reaction notes

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